QuickView for Erythromycin (compound)

Summary
General Info

PubChem

PubChem Compound 10032882

Name:	Erythromycin
PubChem Compound ID:	10032882
Description:	A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.
Molecular formula:	C₃₇H₆₇NO₁₃
Molecular weight:	733.927 g/mol

DrugBank

Identification

Name:	Erythromycin
Name (isomeric):	DB00199
Drug Type:	small molecule
Description:	A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.
Synonyms:	Erythrocin Stearate; Erythromycin Stearate; Erythromycin lactobionate; Erythrocin; Erythromycin oxime; Erythromycin estolate; EM; Erythromycin glucoheptonate; Erythromycin ethylsuccinate
Brand:	Ilotycin Gluceptate, Eryderm, Erythromid, Serp-AFD, Eryc, Erythro, E-Glades, Benzamycin, E-Base, Erygel, Erythromast 36, Benzamycin Pak, Erycinum, Erycin, Ilosone, Erypar, Erythromycin A, Erycette, Erythromycin B, Erythrogran, Erythroguent, Emgel, R-P Mycin, Abboticin, Ilocaps, Taimoxin-F, Aknin, Erymax, Ethril 250, Dotycin, Abomacetin, Erythro-Statin, Wyamycin S, Robimycin, Mephamycin, Erycen, Eryc Sprinkles, Theramycin Z, Stiemycin, Akne-Mycin, ETS, E-Solve 2, Ery-Tab, Pce, Eryc 125, Pantomicina, Ilotycin, Sansac, Dumotrycin, Bristamycin, Ak-mycin, Torlamicina, Ery-Sol, Eritrocina, EMU, Propiocine, Pfizer-e, IndermRetcin, Erythra-Derm, Ermycin, Kesso-Mycin, E-Mycin, Wemid
Brand name mixture:	T-Stat Lot(Alcohol Anhydrous + Erythromycin), Staticin Lot(Alcohol Anhydrous + Erythromycin + Laureth 4), Stievamycin Forte Gel(Erythromycin + Tretinoin), Sans-Acne Solution(Alcohol Anhydrous + Erythromycin), T-Stat Pad-Lot(Alcohol Anhydrous + Erythromycin), Stievamycin Gel(Erythromycin + Tretinoin)
Category:	Anti-Bacterial Agents, Macrolides
CAS number:	114-07-8

Pharmacology

Indication:	For use in the treatment of infections caused by susceptible strains of microorganisms in the following diseases: respiratory tract infections (upper and lower) of mild to moderate degree, pertussis (whooping cough), as adjunct to antitoxin in infections due to <i>Corynebacterium diphtheriae</i>, in the treatment of infections due to <i>Corynebacterium minutissimum</i>, intestinal amebiasis caused by <i>Entamoeba histolytica</i>, acute pelvic inflammatory disease caused by <i>Neisseria gonorrhoeae</i>, skin and soft tissue infections of mild to moderate severity caused by <i>Streptococcus pyogenes</i> and <i>Staphylococcus aureus</i>, primary syphilis caused by <i>Treponema pallidum</i>, infections caused by <i>Chlamydia trachomatis</i>, nongonococcal urethritis caused by <i>Ureaplasma urealyticum</i>, and Legionnaires' disease caused by <i>Legionella pneumophila</i>.
Pharmacology:	Erythromycin is produced by a strain of Streptomyces erythraeus and belongs to the macrolide group of antibiotics. After absorption, erythromycin diffuses readily into most body fluids. In the absence of meningeal inflammation, low concentrations are normally achieved in the spinal fluid, but the passage of the drug across the blood-brain barrier i... show more » Erythromycin is produced by a strain of Streptomyces erythraeus and belongs to the macrolide group of antibiotics. After absorption, erythromycin diffuses readily into most body fluids. In the absence of meningeal inflammation, low concentrations are normally achieved in the spinal fluid, but the passage of the drug across the blood-brain barrier increases in meningitis. Erythromycin is excreted in breast milk. The drug crosses the placental barrier with fetal serum drug levels reaching 5 - 20% of maternal serum concentrations. Erythromycin is not removed by peritoneal dialysis or hemodialysis. show less «
Mechanism of Action:	Erythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterial ribosomes or near the “P” or donor site so that binding of tRNA (transfer RNA) to the donor site is blocked. Translocation of peptides from the “A” or acceptor site to the “P” or donor site is prev... show more » Erythromycin acts by penetrating the bacterial cell membrane and reversibly binding to the 50 S subunit of bacterial ribosomes or near the “P” or donor site so that binding of tRNA (transfer RNA) to the donor site is blocked. Translocation of peptides from the “A” or acceptor site to the “P” or donor site is prevented, and subsequent protein synthesis is inhibited. Erythromycin is effective only against actively dividing organisms. The exact mechanism by which erythmromycin reduces lesions of acne vulgaris is not fully known: however, the effect appears to be due in part to the antibacterial activity of the drug. show less «
Absorption:	Orally administered erythromycin base and its salts are readily absorbed in the microbiologically active form. Topical application of the ophthalmic ointment to the eye may result in absorption into the cornea and aqueous humor.
Protein binding:	Erythromycin is largely bound to plasma proteins, ranging from 75 - 95% binding depending on the form.
Biotransformation:	Hepatic. Extensively metabolized - after oral administration, less than 5% of the administered dose can be recovered in the active form in the urine. Erythromycin is partially metabolized by CYP3A4 resulting in numerous drug interactions.
Half Life:	0.8 - 3 hours
Toxicity:	Symptoms of overdose include diarrhea, nausea, stomach cramps, and vomiting.
Affected organisms:	Enteric bacteria and other eubacteria

Interactions

Food interaction:

Avoid alcohol.

Take on empty stomach: 1 hour before or 2 hours after meals.

Take with a full glass of water Avoid taking with grapefruit juice.

Drug interaction:

Grepafloxacin	Increased risk of cardiotoxicity and arrhythmias
Bretylium	Increased risk of cardiotoxicity and arryhthmias
Levofloxacin	Increased risk of cardiotoxicity and arrhythmias
Carbamazepine	The macrolide, erythromycin, may increase the effect of carbamazepine.
Sparfloxacin	Increased risk of cardiotoxicity and arrhythmias

Grepafloxacin	Increased risk of cardiotoxicity and arrhythmias
Bretylium	Increased risk of cardiotoxicity and arryhthmias
Levofloxacin	Increased risk of cardiotoxicity and arrhythmias
Carbamazepine	The macrolide, erythromycin, may increase the effect of carbamazepine.
Sparfloxacin	Increased risk of cardiotoxicity and arrhythmias
Imatinib	The macrolide, erythromycin, may increase the serum concentration of imatinib.
Eletriptan	The macrolide, erythromycin, may increase the effect and toxicity of eletriptan.
Tamsulosin	Erythromycin, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Erythromycin is initiated, discontinued, or dose changed.
Citalopram	Possible serotoninergic syndrome with this combination
Telithromycin	Telithromycin may reduce clearance of Erythromycin. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Erythromycin if Telithromycin is initiated, discontinued or dose changed.
Lincomycin	Possible antagonism of action with this combination.
Verapamil	Erythromycin, a moderate CYP3A4 inhibitor, may increase the serum concentration of veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Monitor for changes in the therapeutic/adverse effects of verapamil if erythromycin is initiated, discontinued or dose changed.
Tramadol	Erythromycin may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
Methylprednisolone	The macrolide, erythromycin, may increase the effect of corticosteroid, methylprednisolone.
Sildenafil	The macrolide, erythromycin, may increase the effect and toxicity of sildenafil.
Thioridazine	Increased risk of cardiotoxicity and arrhythmias
Lovastatin	The macrolide, erythromycin, may increase the toxicity of the statin, lovastatin.
Alfentanil	The macrolide, erythromycin, may increase the effect and toxicity of alfentanil.
Aprepitant	Erythromycin, a moderate CYP3A4 inhibitor, may increase the effect and toxicity of aprepitant.
Theophylline	The macrolide, erythromycin, may increase the effect and toxicity of theophylline.
Quinidine barbiturate	Increased risk of cardiotoxicity and arrhythmias
Astemizole	Increased risk of cardiotoxicity and arrhythmias
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of erythromycin by decreasing its metabolism. Erythromycin may increase the serum concentration of voriconazole by decreasing its metabolism. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for QTc prolongation and changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose changed.
Itraconazole	The macrolide, erythromycin, may increase the effect and toxicity of itraconazole.
Quinupristin	This combination presents an increased risk of toxicity
Artemether	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Cyclosporine	The macrolide, erythromycin, may increase the effect of cyclosporine.
Quinidine	Increased risk of cardiotoxicity and arrhythmias
Felodipine	Erythromycin increases the effect of felodipine
Disopyramide	Increased risk of cardiotoxicity and arrhythmias
Oxtriphylline	The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, oxtriphylline.
Ritonavir	Increased toxicity of both agents
Digoxin	The macrolide, erythromycin, may increase the effect of digoxin in 10% of patients.
Dihydroergotoxine	Possible ergotism and severe ischemia with this combination
Dofetilide	Increased risk of cardiotoxicity and arrhythmias
Aminophylline	The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, aminophylline.
Dicumarol	The macrolide, erythromycin, may increase the anticoagulant effect of dicumarol..
Repaglinide	The macrolide, erythromycin, may increase the effect of repaglinide.
Mesoridazine	Increased risk of cardiotoxicity and arrhythmias
Methylergonovine	Possible ergotism and severe ischemia with this combination
Thiothixene	May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Clozapine	Erythromycin increases the effect of clozapine
Zafirlukast	Erythromycin may decrease the serum concentration and effect of zafirlukast.
Amiodarone	Increased risk of cardiotoxicity and arrhythmias
Rifabutin	The rifamycin, rifabutin, may decrease the effect of the macrolide, erythromycin.
Sertraline	Possible serotoninergic syndrome with this combination
Eplerenone	This CYP3A4 inhibitor increases the effect and toxicity of eplerenone
Anisindione	The macrolide, erythromycin, may increase the anticoagulant effect of anisindione.
Cisapride	Increased risk of cardiotoxicity and arrhythmias
Bromocriptine	Erythromycin increases serum levels of bromocriptine
Erlotinib	This CYP3A4 inhibitor increases levels/toxicity of erlotinib
Trazodone	The CYP3A4 inhibitor, Erythromycin , may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Erythromycin is initiated, discontinued or dose changed.
Sibutramine	Erythromycin increases the effect and toxicity of sibutramine
Colchicine	Severe colchicine toxicity can occur
Divalproex sodium	Erythromycin increases the effect of valproic acid
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Dihydroergotamine	Possible ergotism and severe ischemia with this combination
Sotalol	Increased risk of cardiotoxicity and arrhythmias
Fluoxetine	Possible serotoninergic syndrome with this combination
Vardenafil	Erythromycin, a moderate CYP3A4 inhibitor, may reduce the metabolism and clearance of vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of vardenafil if erythromycin is initiated, discontinued or dose changed.
Pimozide	Increased risk of cardiotoxicity and arrhythmias
Docetaxel	Erythromycin may increase the serum levels and toxicity of docetaxel.
Alprazolam	The macrolide, erythromycin, may increase the effect of the benzodiazepine, alprazolam.
Vinorelbine	Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vinorelbine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Erythromycin is initiated, discontinued or dose changed.
Buspirone	The macrolide, erythromycin, may increase the effect and toxicity of buspirone.
Rifampin	The rifamycin, rifampin, may decrease the effect of the macrolide, erythromycin.
Tacrolimus	Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. The macrolide antibiotic, erythromycin, may also increase the blood concentration of tacrolimus.
Dyphylline	The macrolide, erythromycin, may increase the effect and toxicity of the theophylline derivative, dyphylline.
Acenocoumarol	The macrolide, erythromycin, may increase the anticoagulant effect of acenocoumarol.
Moxifloxacin	Increased risk of cardiotoxicity and arrhythmias
Atorvastatin	The macrolide, erythromycin, may increase the toxicity of the statin, atorvastatin.
Toremifene	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
Everolimus	The macrolide, erythromycin, may increase the serum concentration and toxicity of everolimus.
Bromazepam	Erythromcyin may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if erythromycin is initiated, discontinued or dose changed. Dosage adjustments may be required.
Cinacalcet	The macrolide, erythromycin, may increase the serum concentration and toxicity of cinacalcet.
Quetiapine	The macrolide, erythromycin, may increase the effect and toxicity of quetiapine.
Cabergoline	Erythromycin increases serum levels and toxicity of cabergoline
Vinblastine	Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the vinblastine serum concentration and distribution in certain cells. Consider alternate therapy to avoid vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of vinblastine if erythromycin is initiated, discontinued or dose changed.
Simvastatin	The macrolide, erythromycin, may increase the toxicity of the statin, simvastatin.
Vincristine	Erythromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vincristine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Erythromycin is initiated, discontinued or dose changed.
Gefitinib	This CYP3A4 inhibitor increases levels/toxicity of gefitinib
Zopiclone	The macrolide antibiotic, erythromycin, may increase the serum concentration of zopiclone. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if erythromycin is initiated, discontinued or dose changed.
Methysergide	Possible ergotism and severe ischemia with this combination
Diazepam	The macrolide, erythromycin, may increase the effect of the benzodiazepine, diazepam.
Midazolam	The macrolide, erythromycin, may increase the effect of the benzodiazepine, midazolam.
Ranolazine	Increased levels of ranolazine - risk of toxicity
Sirolimus	The macrolide, erythromycin, may increase the serum concentration of sirolimus.
Zuclopenthixol	Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Valproic Acid	The macrolide antibiotic, Erythromycin, may increase the serum concentratin of Valproic acid. Consider alternate therapy or monitor for changes in Valproic acid therapeutic and adverse effects if Erythromycin is initiated, discontinued or dose changed.
Ergonovine	Possible ergotism and severe ischemia with this combination
Topotecan	The p-glycoprotein inhibitor, Erythromycin, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
Triazolam	The macrolide, erythromycin, may increase the effect of the benzodiazepine, triazolam.
Cilostazol	Erythromycin increases the effect of cilostazol
Warfarin	The macrolide, erythromycin, may increase the anticoagulant effect of warfarin.
Terfenadine	Increased risk of cardiotoxicity and arrhythmias
Ziprasidone	Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
Trimipramine	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Ergotamine	Possible ergotism and severe ischemia with this combination
Cerivastatin	The macrolide, erythromycin, may increase the toxicity of the statin, cerivastatin.

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Targets

23S rRNA

50S ribosomal protein L22

50S ribosomal protein L4

Enzymes

Transporters

Multidrug resistance protein 1

Multidrug resistance-associated protein 1

Solute carrier organic anion transporter family member 1A2

Solute carrier family 22 member 7